Stability behaviour of antiretroviral drugs and their combinations. 1: characterization of tenofovir disoproxil fumarate degradation products by mass spectrometry

Kurmi, Moolchand; Golla, Vijaya Madhyanapu; Kumar, Sandeep; Sahu, Archana; Singh, Saranjit

doi:10.1039/c5ra17532a

Cited by 25 publications

(28 citation statements)

References 13 publications

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“…S1), similar to degradation product of the drug reported in the literature [17][18][19], and hence was identified as 5-fluoro-1-((2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5yl)pyrimidine-2,4(1H,3H)-dione. The structure of this product, along with degradation products of TDF reported by us earlier [15], are shown in Fig. 1.…”

Section: Degradation Of Ftc In Solid Statementioning

confidence: 95%

“…The released isoproxil moieties were further degraded to isopropyl hydrogen carbonate, generating formaldehyde in the process [15]. In this study also, degradation products of TDF, viz., T1 and T6 were seen under solid state conditions, of course along with T7, T8, T11 and T12 (Fig.…”

Section: Postulated Interaction Pathway Of Ftc and Tdfmentioning

confidence: 99%

“…Solid state degradation study on TDF was carried out by us previously and is reported in the first part of this series [15]. Therefore, solid state degradation study in this investigation was restricted to FTC alone.…”

Section: Solid State Degradation Studies On Ftcmentioning

confidence: 99%

“…This study, which is third in the series on stability-related aspects of anti-retroviral drug combinations [15,16], explored solid state interaction behaviour of FTC and TDF. A total of six interaction products (FT1-FT6), along with degradation products of individual drugs, got separated by high performance liquid chromatography (HPLC) using a C18 column as the stationary phase.…”

Section: Introductionmentioning

confidence: 99%

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Stability behaviour of antiretroviral drugs and their combinations. 3: Characterization of interaction products of emtricitabine and tenofovir disoproxil fumarate by mass spectrometry

Kurmi

Singh

Tiwari

et al. 2016

Journal of Pharmaceutical and Biomedical Analysis

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The present study investigated drug-drug interaction behaviour of emtricitabine (FTC) and tenofovir disoproxil fumarate (TDF) under solid state stability test conditions. Six interaction products were separated and detected by high performance liquid chromatography coupled to photodiode array detector (HPLC-PDA) using C18 column. The same were characterized using LC-high resolution mass spectrometry (LC-HRMS), LC-multi stage mass spectrometry (LC-MS(n)) and online hydrogen/deuterium (H/D) exchange studies. The interaction pathway among the two drugs was outlined based on the elucidated structures. Four of the six interaction products were also formed in marketed tablets containing FTC and TDF (along with efavirenz (EFV)) that were kept without packing under accelerated condition of 40°C/75% RH till 6 months.

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Section: Degradation Of Ftc In Solid Statementioning

confidence: 95%

Section: Postulated Interaction Pathway Of Ftc and Tdfmentioning

confidence: 99%

Section: Solid State Degradation Studies On Ftcmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Stability behaviour of antiretroviral drugs and their combinations. 3: Characterization of interaction products of emtricitabine and tenofovir disoproxil fumarate by mass spectrometry

Kurmi

Singh

Tiwari

et al. 2016

Journal of Pharmaceutical and Biomedical Analysis

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“…The elucidation of the mass fragmentation pathway of the drug was achieved with the help of MS/TOF. The studies were performed in ESI positive mode (Kurmi et al, 2015;Singh et al, 2013). The instrument parameters were irst optimized to get the molecular ion peak of the drugs.…”

Section: Ms Studies On the Drugsmentioning

confidence: 99%

Solution state stress degradation studies of antifilarial drug albendazole

Nanda

Bajaj

2019

ijrps

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This study was conducted to explore the stress degradation studies of anti ilarial drug albendazole (ALB) in the solution state. The stress conditions targeted were hydrolytic (acidic, neutral, and basic) as well as oxidative. The drug was degraded under different concentrations of stressor and the time of exposure. All the degraded samples were then subjected to reversed-phase highperformance liquid chromatography using photodiode array (HPLC-PDA) as a detector. The inal concentration of stressor, as well as the duration of exposure for each condition, were optimized from the results. The method optimization was done on a C18 stationary phase with a varying mobile phase composition. The parameters of the mobile phase varied were organic modiier, buffer (type and concentration) and gradient as well as run time. The optimized method included acetonitrile as an organic modi ier, 10 mM potassium dihydrogen orthophosphate (pH 3.0) as a buffer that was pumped in a gradient mode, and run time was ixed at 57.00 min. The samples were further characterized by subjecting to instrumental technique Liquid Chromatography High-Resolution Mass Spectrometry (LC-HRMS). The results highlighted the degradation products formed under the study conditions. Some of the degradation products were common to all hydrolytic conditions, but some were seen only under oxidative conditions.

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Determination of enantiomeric impurity of tenofovir disoproxil fumarate on a cellulose tris(3,5‐dichlorophenyl‐carbamate) chiral stationary phase and the characterization of its related substances

Nguyen

Mai

et al. 2021

J of Separation Science

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A simple and reliable high-performance liquid chromatography method was developed to determine the enantiomeric impurity of tenofovir disoproxil fumarate, an orally bioavailable prodrug of tenofovir, commonly used for the treatment of human immunodeficiency virus and hepatitis B. Tenofovir disoproxil and its enantiomer, were completely separated on a Chiralpak IC column (3 μm, 100 × 4.6 mm, i.d.). The chiral separation was achieved using a mobile phase containing n-hexane, ethanol, methanol, and triethylamine 65/25/10/0.1 (v/v/v/v) at a flow rate of 0.6 mL/min. Ideally, the reversal of enantiomer elution order was achieved on the Chiralpak IC column, to allow the elution of the minor enantiomeric impurity before the major component. Moreover, the proposed method was able to discriminate the active ingredient from the related substances available in the tenofovir disoproxil fumarate raw materials. These compounds were isolated and structurally elucidated by MS and nuclear magnetic resonance. Based on the spectral data, the structures of related substances were confirmed as tenofovir isoproxil monoester and fumaric acid.The high-performance liquid chromatography method was optimized by the design of experiment approach and successfully validated following the International Conference on Harmonization guideline. Proposed method was effectively applied for the quantification of enantiomeric impurity in tenofovir disoproxil fumarate raw materials.

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Stability behaviour of antiretroviral drugs and their combinations. 1: characterization of tenofovir disoproxil fumarate degradation products by mass spectrometry

Abstract: The investigation established the intrinsic degradation behaviour of tenofovir disoproxil fumarate in solid and solution states.

Cited by 25 publications

References 13 publications

Stability behaviour of antiretroviral drugs and their combinations. 3: Characterization of interaction products of emtricitabine and tenofovir disoproxil fumarate by mass spectrometry

Stability behaviour of antiretroviral drugs and their combinations. 3: Characterization of interaction products of emtricitabine and tenofovir disoproxil fumarate by mass spectrometry

Solution state stress degradation studies of antifilarial drug albendazole

Determination of enantiomeric impurity of tenofovir disoproxil fumarate on a cellulose tris(3,5‐dichlorophenyl‐carbamate) chiral stationary phase and the characterization of its related substances

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